Methods of applying soil-release compositions to textile materials

ABSTRACT

TEXTILE MATERIALS CONTAINING SUBSTANTIAL PROPORTIONS OF CELLULOSIC AND/OR HYDROPHOBIC CONSITUENTS ARE PROVIDED WITH BOTH DURABLE-PRESS AND SOIL-RELEASE PROPERTIES BY DEPOSITING ON SAID TEXTILE MATERIALS ACID CATALYZED DURABLEPRESS RESIN PRECURSOR; POLYETHER DERIVATIVE SELECTED FROM THE GROUP CONSISTING OF POLYALKYLENE GLCOLS, THE MONOAND DI-FATTY ACID ESTES OF POLYALKYLENE GLYCOLS, AND THE MONO- AND DI-ALKYL ETHERS OF POLYALKYLENE GLYCOLS, AND THEIR MIXTURES; FLUOROCARBON POLYMER, AND A CATALYTIC QUANTITY OF ACIDIC CATALYST. THE FLUOROCARBON POLYMER CONTAINS HIGHLY FLUORINATED OLEPHOBIC AND HYDROPHOBIC PORTIONS AND NONFLUORINATED HYDROPHILIC PORTIONS.

United States Patent 01 lice 3,598,514 Patented Aug. 10, 1971 3,598,514 METHODS OF APPLYING SOIL-RELEASE COM- POSITIONS TO TEXTILE MATERIALS Stephen B. Sello, Cedar Grove, Ildo Emil Pensa, Palisades Park, and Bipinchandra R. Shukla, East Paterson, N.J., assignors to J. P. Stevens and Co., Inc., New York, N.Y. No Drawing. Filed Feb. 27, 1969, Ser. No. 803,045 Int. Cl. D06m 13/12 Claims U.S. Cl. 8-115.6

ABSTRACT OF THE DISCLOSURE This invention concerns improved methods and compositions for imparting soil-release characteristics to textile substrates which are to have a durable-press or permanent-press finish.

More particularly, this invention relates to compositions comprising fluorocarbon polymers and polyether derivatives, which when used in conjunction with durable-press resin precursors, catalysts and optional textile adjuvants, produce a finish having good soil-release upon one laundering, without compromising the durable-press finish.

With the advent of wash-and-wear, durable-press or permanent-press garments, the utilization of synthetic fibers and their blends with cellulosics and/or other natural fibers has become widespread. Garments containing substantial quantities of polyesters and other hydrophobic fibers have been particularly favored because they strengthen the abrasion resistance of cellulosic based garments and increase the crease resistance of the garments without the need of an increased amount of cross-linking resins. Unfortunately, garments containing a substantial quantity of these synthetic fibers (as illustrated by polyester) have exhibited a pronounced tendency to retain soil and stains, particularly oily stains. Furthermore, these fabrics or garments have been found to resist release of the soil or stains even upon exposure to repeated laundering. In all likelihood the propensity of these blends of synthetic and natural fiber to accumulate stains is due to the inherently oleophilic structure of synthetics such as polyester.

Increased resistance to the release of soil and stains also results from the crosslinking resins employed to impart durable-press properties to fabrics. These resins are probably converted during their insolubilization to oleophilic structures. Whatever the factors that are involved, soil and stain retention in fabrics treated with thermoset crosslinking resins has been a serious and costly problem.

U.S. Pat. No. 3,377,249, discloses a process for imparting soil release finishes to textile materials containing polyester fibers. The claimed process comprises applying an aminoplast textile resin and a synthetic acid emulsion polymer and curing the textile resin to impart the desired finish.

The finishing system of the above patentee is deficient an important aspect, namely, that at least two launderings are required to remove oily soil or stains.

In order to overcome this problem, applicants have developed a finishing system for textiles which contains relatively small quantities of fluorocarbon polymers-and. certain polyether derivatives. The finishing system also includes durable-press resin precursors such as are disclosed in the U.S. Pat. No. 3,377,249. Not only are initial soilrelease properties excellent, but the finish is durable, crease retention is excellent and the hand of the finished product is satisfactory. Inasmuch as the improvement in soil release upon one laundering is obtained at application levels where the individual components of the finish (fluorocarbon polymer and polyether derivative) are inefiective in removing lubricating oil type of stains, the results are most unexpected. Even more startling, good initial and longterm soil release have been obtained in the complete absence of the acrylic acid type polymer component of the soil-release finish said by U.S. Pat. No. 3,377,249 to be critical to acceptable soil release. In view of this, appli cants invention is contrary to the teaching of the prior art.

In practicing the present invention, samples of the textile substrate are treated with a composition comprising durable-press resin precursor, fluorocarbon polymer, polyether derivative, textile adjuvants and necessary catalysts to obtain the desired pickup level. The treated samples are dried between about 60 C. to 130 C., desired configurations imparted therein and the configured samples set by exposure to heat and pressure. The setting step is followed by curing at a sufliciently elevated temperature and for a sufiiciently long time to cure the durable-press resin precursor. The cured substrate has long-lasting durablepress and soil-release properties.

In preferred practice, the textile substrate is padded in an aqueous bath comprising 0.1 to 2% by weight of fluorocarbon polymer, 3 to 15% by weight of polyether derivative, 4-20% by weight of durable-press resin precursor and 0.1 to 5% by weight of acid catalyst. After padding, the treated substrate is passed through squeeze rollers set at about 30-50 lbs/sq. inch so that the desired add-on of each component (based upon the weight of the sub.- strate) is present upon drying. The substrate is then dried at about C. to C. until a moisture content of from about 2 to 11% by weight moisture is obtained. The substrate is placed in the desired configuration and then pressed and cured using the conditions commonly employed in producing creased durable-press garments.

While it is convenient to apply all the components of the padding bath simultaneously, the components can be applied separately or in more than one bath.

The fluorocarbon polymers which are an essential component of the soil-release compositions of this invention contain highly fluorinated oleophobic and hydrophobic portions and nonfluorinated hydrophilic portions. Preferably, the highly fluorinated portions contain perfluoroalkyl groups of at least 4 carbon atoms and the nonfluorinated portions contain groups of the formula {-C H 0-} where x is an integer of 1 to 4 and e is an integer of 4 to 20. Illustrative of suitable fluorocarbon The following are specific illustrations of the preferred polymers are: fluorocarbon monomers:

(a) A homopolymer of a monomer of the formula wherein 5 C H R; is a fiuoroalkyl radical contammg 4 to 25 carb 3 7 H atoms such as CaFnS OzN(CHzCHzO)1aCCH=CH-,y

l 02115 $153 z 1 GF)m 10 CtF SOzN(CH2H O)mG=CH OH F elm wherem ovrmso,N oHzoH20515o(0,11, ;011, I

Z is H or F, and m is an integer ranging from 3 to 24,

X 2} difunctional radical Selected from the group The polyether derivatives suitable for the soil-release Slstmg of 1 compositions include polyalkylene glycols (such as poly- I I I ethylene and polypropylene glycols), the monoand di- CONGO-and fatty acid esters of polyalkylene glycols (such as the monoand di-oleates and stear ates ofpolyethylene glycol) whervelvn and the monoand di-alkyl ethers of polyalkylene glycols R is lower alkyl (from 1 to 4 carbon atoms), (such as the monoand dimethyl and ethyl ethers of b is an integer ranging from 0 to 15, polyethylene glycol). g ranges from about 1 to The textile substrates used in the present invention are e i an integer ranging f 4 t 20, textile materials containing substantial quantities of na- G i an unsaturated l di l tural and/or synthetic hydrophobic thermoplastic mate- 0 rials in the form of yarns, slivers, filaments, tows, fibers, 3 articles, garments and the like produced by processes such as drawing, spinning, combing, weaving, knitting, needlewherein punching or other non-weaving procedures. Illustrative of these substrates are cellulosics such as cotton; and synthetic R 1s an unsaturated aliphatic radlcal containing from polymers such as polyesters polyamides, polyethylene 2 to 8 carbon atoms and polypropylene, polyacrylonitrile or blends of these cellu- Y is -C H O h i x i an i t ranging f losics and synthetics. The process has considerable utility 1 to 4, and in imparting a soil-release finish to textile materials containing at least 25% by weight of these synthetics, usually (b) Copolymers from 50% by weight and upwards. The favored synthetic R X-[Y] G substrate is polyester such as poly(ethyle ne terephthalate) wherein and poly(l,4-cyclohexylene-dimethylene terephthalate).

When the substrate comprises 100% by weight of synthetic fibers the dunable-press resin precursor can be omitted.

Durable-press characteristics are obtained by the use of acid catalyzed durable-press resin precursors which can Rf, X, G, e and Y are as defined above, with at least one of vinylic monomers such as vinyl chloride, vinyl acetate, ethylene, propylene, acrylic acid, methacrylic acid, acrylate or methacrylate esters, fluorinated acrylic zi f gi jggi i fig g ggz of polyethylene be generically grouped as adducts of formaldehyde with amides. The products can be linear or cyclic in structure or (c) Commercially available fluorinated polymer having they can comprise mixtures of one or more of these strucan average composition represented by the formula tural types. These precursors can be aliphatic, aromatic Outstanding results are obtained with fluorocarbon or heterocyclic. A listing of preferred resin precursors polymers prepared from monomers of the formula: includes:

2 n N ,N ,N -tris(hydroxymethyl)melamine, RSO2N(CHZCHZO)GOCR=CRZ hexakis(methoxymethyl)melamine, wherem the bis (hydroxymethyl) triazolidinones, R, is a perfluoroalkyl radical having 6 to 10 carbon Y Y YU atoms, 1,3 -bis (hydroxymethyl) -2-imidazolidinone, R is hydrogen or lower alkyl having from 1 to 6 carbon Y Y- y Y l/ atoms imldazolidinone, d ranges from about 12 to 20, and NiN1'biS(meth0XymethY1)I011, 3 and 4 are Selected f the group. consisted f Z-methoxyethyl N,N-bis(hydroxymethyl)carbamate and hydrogen and lower alkyl having from 1 to 4 carbon dHHethYIOIdihYdTOXY ethylene urea, among Othersatoms.

Preferred acidic catalysts forsaid resin precursors in-v The fluorocarbon P y f be P PP followlng clude metal salts suchas magnesium chloride, zinc nitrate known Procedures Such as dlsclosed 1n the following and Zinc fluoroborate'; and amino salts such as monoethpatents.U.S.: 2,732,398; 2,803,615; 2,915,554; British: anolamine hydrochloride and Z-amino-Z-methylpfopanol 857,689. nitrate. I

The various modifiers, agents, conditioners and acids which alter characteristics other than durable press and stain release of the finished textile products are generically categorized as textile adjuvants. These adjuvants include softeners, surfactants, hand modifiers, antistatics, thickeners and the like. Illustrative of these are polyvinyl acetates of various average molecular weight ranges, thickeners such as the natural gums, ethylated starches, hydroxyethylcellulose and sodium carboxymethylcellulose, among others. Also intended to be included as adjuvants are the various wetting agents and other surfactants such as p l,1,3,3 tetramethylbutyl)phenoxynona(ethyleneoxy)-ethanol, the sodium salt of N-methyl-N-oleyltaurine, and the sodium salts of sulfonated hydrocarbons, among others. Since the role of the textile adjuvants is not critical to the inventive process, no attempt has been made to present an exhaustive or even lengthy list. Voluminous listings of the many textile adjuvants can be found in commercial brochures, chemical literature and in the soap and chemical specialties listings of the Department of Agriculture.

All of the constituents of the process of this invention can be applied to the textile substrates by any of the conventional impregnation methods known in the textile art. These include the preferred padding or dipping method, as well as spraying, coating, or the like. The polymeric treating compositions can be in the form of a solution where the solubility characteristics allow it, or in the form of an emulsion or dispersion. Preferably, the textile substrate is dipped into a bath which is an aqueous dispersion of the components to be applied.

The concentrations of the treating agents employed are varied to some extent according to the effect sought, the type of substrate, and the weight of the substrate. The following data show the ranges of components to be added in terms of parts by weight per 100 parts by weight of original fabric (this basis for indicating the weight of finish component added being hereinafter referred to as Percent Solids OWF) Percent solids OWF Suitable Preferred Component range range Fluorocarbon polymer 0. 1-3. 0. 15-0. Durable-press resin precursor 8 0-20. 0 5. 0-10. 0 Polyether derivative 2. 0-15. 0 3. 0-8. 0 Acid catalyst 0. 1-20. 0 0. 2-6. 0

plished using different combinations of temperature, time and pressure. For instance, the treated fabric after being made into a garment can be pressed on an electrically heated hot-head garment press as follows: Steam is used for the first 5 seconds (at 150 to 160 C.), then the temperature is raised between about 160 C. to 250 C. keeping the head pressure at about 85-100 pounds/sq.

inch. After the final heating, vacuum is applied for from about 3 to 15 seconds or higher to complete the pressing operation. Curing is accomplished by heating between about 130 C. to about 200 C.

If desired, the setting operation can be accomplished in a garment-setting even using comparable temperatures and times. Again as the mode of pressing and setting the creases or pleats is not novel nor critical to the invention, no attempt will be made to described them in detail.

In order to illustrate the invention as completely as possible, the accompanying examples are submitted. Unless otherwise specified, all percentages are expressed on a weight basis. A description of the test methods and the terms used in the examples precedes the examples.

EVALUATION OF SOIL RELEASE The following soiling agents were used, denoted respectively as-vegetable oil (V), mineral oil (M), and lubricating oil (L):

Corn oil.--(Not hydrogenated); e.g., Mazola, Best Foods Division, Corn Products 'Co., New York, N.Y.

Extra heavy mineral oil.Saybolt viscosity between 360 and 390 at F., specific gravity between 0.880 and 0.900 at 60 F.; e.g., Nujol, Plough, Inc., New York, N.Y.

Used, dirty lubricating oil.Drained from the crankcase of an automobile.

The fabric specimen, no smaller than 18 by 15 inches, was laid on a glass plate covered by polyethylene film 3 inches square. The soiling agent was applied to the face side, using 4 drops (0.25 ml.) when in liquid form. A 1.2 ml. (0.25 teaspoon) portion is spread as a circular spot approximately 2.4 cm. in diameter, but not worked into the fabric. Polyethylene film 3 inches square was placed over the spotted area immediately, and a 2.5- inch diameter, 5-pounds weight was left over each spot for 30 seconds to impart a pressure of approximately 1 pound per square inch. Then the original polyethylene films were discarded, and the specimen was sandwiched between two paper towels, the sandwich having been covered top and bottom with polyethylene film to prevent soiling the glass plate and the weight. The S-pound weight was then placed over the spotted area for 3 seconds to blot out excess soiling agent. (If excess soiling agent remained, it was removed at once by lightly blotting with a facial tissue.) Next, stained specimens were aged in the ordinary room atmosphere for at least 30 minutes by being hung so there was no contact between specimens.

Laundering was done in a home-type washer at approximately 50 C. in S-pound loads using the high water level (16 gallons) with a level cupful of non-ionic detergent, and tumble dried.

Rating for residual soil used the Deering Milliken Photographic Standards for Evaluation of Soil-Release Finishes, the scale of which is from 1 to 5. No visible spot remaining was denoted by 5, and a spot barely visible by 4, with 3, 2, and 1 denoting progressively serious strains. The evaluation was made under ordinary overhead fluorescent room lighting of normal intensity with the test specimen flat on a table top 35:1:5 inches from the floor directly under the light, and viewed from all possible angles. The rating for each stain was the lowest number assigned it from any angle. Evaluation of wash and wear.-AATCC 88A-1964T Test IH-C for laundering: Home-type washer, S-pound load, full cycle, 60 C., synthetic detergent; tumble drying (TD). The number of laundering-drying cycles (as 1, 2 or 5 is indicated in tables by 1L, 2L, or SL. The S-point rating scale extend from 1 (extensively wrinkled) to 5 (prefectly smooth).

Evaluation of crease retention.-AATCC 88A-1964T Test III-C also. The rating scale is as follows: 1. (no crease remaining), 2. (slight crease), 3. (moderate crease), 4. (sharp crease), and 5. (unchanged, very sharp crease) OWB.-Means on the weight of the bath used for padding in percent.

Percent Solids OWF.Means parts by weight of finishing component added per hundred parts by weight of original fabric.

WPU.Means wet pickup or percent add-on, i.e.,

Weight of wet add-onx 100 Weight of original fabric 7 8 EMBODIMENT A bake and seconds vacuum. Finally, the durable-press finish was cured by heating at 165 C. for minutes. A monomer havmg the structure The wash-and-wear, crease-retention :and soil-release 0 data obtained through the use of the individual soil-rel 5 lease components appear in Table 1. The term Stained CamsO2N (CH=OHO)ACH CH after 5L indicates that after the finishing system was is prepared by the methods described in US. Pats. 2,803,- applied, the sample was laundered five times before be- 615 and 2,915,554. ing stamed.

TABLE 1 Soil release Percent OWF Original stains Stained after 5L. Fluoro- Wash carbon MME and Crease 1L 2L 1L 2L polymerof wear retention active PEG PEG (5L-TD) (5L-TD) V L V L V L V L l The fabric also contained dimethylol dihydroxy ethylene urea (5.7% solids OWF) with zinc nitrate (0.6% solids OWF). Nora-Fabric used: 50/50 polyester/cotton blend twist twill dyed (spruce).

In preparing this monomer, the alcohol As can be seen from the data in Table l, the individ- C3H7 ual components of the soil-release composition (fluoro- H carbon polymer and the polyether additives) are rela- CSFTSOZDTTwHfiHZOm tively ineffective in providing a durable stain-release fin- 8 m In accordance With the Procedures of e ish that releases oil stains upon one laundering but per- 2,915,554 and this alcohol is reacted wlth acrylic acid In sists upon t d laundering. The subsequent examples accordance With the Procedures of 2,803,615- establish the synergistic effect that is obtained when the The mchcmef is emulsion polymerized y the method fluorocarbon polymer and alcohol additive components scribed in Example 1 of US. Pat. 2,803,615. The reaction are combined mixture is cooled and worked up by the described techniques to yield a polymer latex having a solids content of about 36% solids.

EXAMPLE 2 A soil-release composition comprising mixtures of fluoro- EXAMPLE 1 carbon polymer and the monomethyl ether of poly- Unsuccessful attempts to impart a durable soil-release finethyle glycol ish using the individual components (fluorocarbon poly- The fabric Substrate used f or treatment isthe same mer and polyether derivative) of the soil-release fiIllSh one employed in Example 1 Pad baths are made p The substrate used for treatment is a fabric blend of 40 containing two different concentrations of the fluoropolyester by weight) and cotton (50% by weight) carbon polymer of Embodiment A and two different having a thread count (warp x filling) of 134 x 66, dyed concentrations of the methyl ether of polyethylene glyspruce green in color. col, molecular weight 860. Each pad formulation also The following application procedure was used. Aquecontained 1.0% OWB zinc nitrate catalyst and 9.5% ous pad baths were made up containing varying amounts OWB dimethylol dihydroxyethylene urea resin precursor. of the individual components of the soil-release compo- The samples were padded,dried, framed, cut, creased, sition, the fluorocarbon polymer described in Embodipressed and cured as in Example 1. The data obtained ment A and different polyether derivatives, 1 plus dlmethon each of the fabric samples relating to wash-and-wear, yloldihydroxyethylene urea resin (9.5% solids OWB) 50 crease retention and soil release (both originally and and 1.0% solids OWB of Zn(NO catalyst. The fabric upon restraining) appear in the accompanying Table 2. samples were padded through squeeze rolls set to give It should be noted that combining the fluorocarbon polyawet pickup of about mer and the polyether additive results in a synergistic After padding, the fabric sample was framed to the increase in durability of the soil release as compared to original dimensions and dried at approximately 125 C. that of the individual components shown in Example 1.

TABLE 2 Soil release Original stains Stained after 5L Percent OWF 1 Wash 1L 2L 1L 2L Fluoro- Monomethyl and Crease carbonpolyether of wear retention V L V L V L V L mer-active PEG (EL-TD) (BL-TD) 0.18 5.4 4.0 4.0 5 5 5 5 3 4 4 4 5 0.14 5.4 4.0 3.5 5 5 5 5 4 3/4 5 4 5 0.18 3.6 3.5 4.0 5 2 5 2 3 3 4 a 4 4 0.14 a5 4.8 4.5 5 2 5 3 4 a 5 4 1 Same concentration of dimethylol ethylene urea and zinc nitrate as in Example 1.

for 5 minutes. The dried fabric is cut into samples desig- EXAMPLE 3 Hated as Shown m Table Each samp 16 was Pressed Wlth A soil-release finish utilizing a mixture of fluorocarbon a crease in it on a garment press set at lbs./sq. inch using the following cycle of 5 seconds steam, 10 seconds 218 polmer and polyethylene glycol MW 660 In this example the same polyester-cotton fabric sub- Polyethylene glycol (PEG) molecular weight 660,:1ndt strate, durable-press resin precursor, acid catalyst and monometh l ether of 01 eth lone 1 col MME' of PEG m01ecu1 aryweigmtv660 p y y g y 7 fluorocarbon polymer used in the precedlng examples were used. Padding, framing, drying, cutting, creasing, pressing and curing were identical to those described in Examples 1 and 2. The concentration of the durablepress resin precursor and zinc nitrate catalyst in the bath (OWB) are identical to Examples 1 and 2. However, polyethylene glycol MW 660 was used as the polyether derivative.

As can be seen by the accompanying table, excellent and durable soil release was obtained using the synerin providing a durable soil-release finish, combining the same components apparently creates a synergistic mixture which imparts an effective and durable finish to the treated substrate.

As this specification discloses, numerous modifications and changes in constituents, temperatures, concentrations, substrates and the like can be made without departing from the inventive concept. The metes and bounds of this invention are best determined by the claims which gistic mixture of the soil-release components. 10 follow, read in conjunction with the specification.

TABLE 3 Soil release Percent OWF 1 Original stains Stained after 5L Fluoro- Polyethyl- Wash carbon one glycol and Crease 1L 2L 1L 2L polymer- (Carbowax weal retention active 1540) (5L-TD) (BL-TD) V L V L V L V L Norm-See footnotes bottom of Table 1.

EXAMPLE 4 5 We claim:

Soil-release compositions utilizing the fluorocarbon polymer durable-press resin precursor, acid catalyst of Examples 1 to 4 admixed with different polyether derivatives Pad bath formulations are prepared containing OWB:

9.5% dimethyloldihydroxyethylene urea 1.0% fluorocarbon polymer of embodiment A 1.0% zinc nitrate, and 10% of the following polyether derivatives:

Monooleate of polyethylene glycol 660 Monooleate of polyethylene glycol 860 Monooleate of polyethylene glycol 1260 Monooleate of polyethylene glycol 3610 Dioleate of polyethylene glycol 1070 Dioleate of polyethylene glycol 3870 Monostearate of polyethylene glycol 3610 Distearate of polyethylene glycol 3870 Padding, wet pickup, drying, framing, sampling, creasing, pressing, etc. are identical to the preceding examples.

In each instance, good, durable soil-release finishes are obtained which do not impair the durable-press finish.

As the preceding discussion and examples indicate, the results obtained by the practice of this invention are both advantageous and unexpected.

For example, both durable stain release are obtained in fabrics and garments containing natural or synthetic fibers or their blends. Furthermore, unlike the soil-release compositions claimed in US. Pat. No. 3,377,249 to Marco, oily soil can be completely removed in a single laundering rather than requiring several launderings. In addition neither the quality or durability of the durablepress finish is compromised by the novel soil-release finishes of this invention.

The finding that effective and durable soil-release finishes could be obtained by treatment with compositions free from acrylic acid type polymers was particularly surprising in view of the disclosure of the recently issued Marco patent, which teaches that not only are acrylic acid type polymers required, but that compositions containing less than by weight of acrylic acid type components were ineffective and commercially unacceptable. This fact, coupled with applicants finding that complete soil release of oily stain could be effected in only one laundering as compared to the several required by Marco, was wholly unexpected. A further unusual aspect to applicants invention is the discovery that while the individual components of the soil-release finish, fluorocarbon polymer, polyether derivative are individually ineffective 1. A process for imparting both soil-release and durable-press characteristics to a fabric containing a blend of cellulosic and polyester fibers, said process comprising applying to each parts by weight of said fabric (1) from about 0.1 to 3.0 parts by weight of a fluorocarbon homopolymer wherein said fluorocarbon homopolymer is prepared from a monomer of the formula wherein R f is a perfluoroalkyl radical having 6 to 10 carbon atoms,

R is hydrogen or alkyl of from 1 to 6 carbon atoms,

d is an integer of from 12 to 20, and

R and R are selected from the group consisting of hydrogen and lower alkyl having from 1 to 4 carbon atoms.

(2) from about 2 to 15 parts by weight of at least one polyether derivative selected from the group consisting of'polyalkylene glycol and esters, and ethers of said polyalkylene glycol,

(3) from about 3.0 to 20 parts by weight of an acid catalyzed durable-press resin precursor which is an adduct of formaldehyde and an amide, and,

(4) from about 0.1 to 5.0 parts by weight of an acidic catalyst for said durable-press resin precursor, and

heating the textile material until the durable-press resin precursor is cured and a soil-release and durable-press finish is imparted tothe fabric.

2. A process as claimed in claim 1 wherein the polyether derivative is polyethylene glycol, a fatty acid ester of polyethylene glycol or an alkyl ether of polyethylene g ycol.

3. A process os claimed in claim 1 wherein said durable-press resin is cured by heating at a temperature of about C. to 200 C.

4. A process as claimed in claim 1 wherein 0.15 to 0.5 part by weight of fluorocarbon homopolymer are applied to each 100 parts by weight of textile material.

1 1 5. A process as claimed in claim 3 wherein said fluoro- References Cited carbon homopolymer is a homopolymer of a monomer UNITED STATES PATENTS having the formula 1 2,915,554 12/1959 Ahlbrecht et a1. 260-86.1X Cam 0 3,377,249 4/1968 Mario 260-29.4UXL 5 3,462,296 8/ 196-9 Raynolds et a1. 260--29.6X

CaFnSOzN(CHzCHz0)m CH=GH JULIUS FROME, Primary-Examiner and said polyether derivative is selected from the group 1 B. LOWE, Assistant Examiner consisting of polyethylene glycol, monomethyl ether of polyethylene glycol, monooleate of polyethylene glycol, 10 U S L dioleate of polyethylene glycol, monostearate of polyethylene glycol and distearate of polyethylene glycol. 260 29'4UA 29'6F 

